Green’s Dictionary of Slang

(US) any kind of footwear; also used fig. as (walk a mile) in my moccasins, to experience my life.

1894		F.P. Dunne in Schaaf Mr Dooley’s Chicago (1977) 182: He’s th’ la-ad that have made th’ Prince iv Wales thrimble in his moccasins.
1903		A. Adams Log of a Cowboy 379: My little pattering feet...will require fifteen-dollar moccasins.
1913		L. Light Modern Hobo 38: I put on my moccasins.
1924		W. James Drifting Cowboy (1931) 17: I’ll be dag-gone if I didn’t catch myself wishing I was in his warm moccasins.
1981		(con. 1900s) A.B. Facey Fortunate Life 43: He noticed my bag boots and asked me why I was wearing moccasins [...] he told me that ‘moccasins’ was the name of the type of boots.
2002		Senator Sanders ‘Senate Sketches #796’ 27 Aug. on Aladems.org Alabama Democratic Party 🌐 There is a saying attributed to Native Americans similar to these words, ‘Don’t criticize how I walk until you have walked a mile in my moccasins.’ I wish you could walk just a quarter mile in the moccasins of those who really struggle to effect economic development in the poor, rural and left out Alabama Black Belt.